Methanol → HCID 18953304, compound

HRID 1491577Notes

Reaction equation

HRID 1491577 reaction equation
[Cl:1][C:2]1[C:3]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].[CH3:19]O.S(=O)(=O)(O)O>O>[Cl:1][C:2]1[C:3]([S:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([O:7][CH3:19])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 13313395HCID 13313395, compound

Product 1

HCID 18953304HCID 18953304, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,4-dichloro-2-phenylsulphenylbenzoic acid (25.0 g), methanol and concentrated sulphuric acid (5 ml) was heated at reflux for 22 hours. Water was added and the mixture concentrated. The residue was taken up in ethyl acetate, washed with aqueous sodium bicarbonate, dried over anhydrous magnesium sulphate and filtered. The solvent was evaporated and the oil purified by chromatography on silica, using a mixture of cyclohexane, ether and toluene to give methyl 3,4-dichloro-2-phenylsulphenylbenzoate (13.8 g) as a clear oil, 1H NMR (CDCl3) 3.7 (3H,s), 7.1 (SH,m), 7.4(2H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 hours
  3. concentrationthe mixture concentrated
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customthe oil purified by chromatography on silica
  9. additiona mixture of cyclohexane, ether and toluene

Sources & evidence

ORD record
ord-b08d16e5793f4eb0a848dc567e689a99
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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